Straight Sissy

Gay guy and his straight sissy slut. Both sharing our content. feel free to message any requests. DM’s always open. Gay is Dom Straight is Sissy.

[Straight Sissy @sissy_guy]

When you can’t resist being a naughty slut…

[chastity dream 220K @MissEvaNavi]

This toy usually goes around the shaft, so I had to improvise. He was allowed to cum...

[My Sissy Fantasy @MySissyFantasy]

It's time to let go of that manhood 💋

#sissy #sissycaption #sissyslut #femboy #crossdresser #slut #transgender #transgirl #feminine

[Ashley Barron @AlsoAshleyB]

Softness is not just in the reflection.

[Goddess Kendra 👠 Sissy School 🏫 @perfectsissys]

Ready to enroll as my sissy student and accomplish your sissy task and assignments for me ?
Dm me now sissy boy 🌸😈

[Mads x Myles @MadsxMyles]

I think this strap is much easier to manage right?

[Proudmaleslave 🇺🇦🥥🌴 @proudmaleslave]

Pure happiness 🥰👸🙏🔥❤️

[Jade malice @jade_malice]

Short Story:
He was missing something physical, but I am not unlocking him, so how about some gentle slapping to the balls with a crop. Still can't believe it actually made him hard 🤭 ... POV story below

Long Story:
He's getting seriously desperate, but I am still not unlocking the cage. He told me he's missing the feeling of something physical more than the orgasm itself. Well, would you look at that, I have a thing just for that. I've read some captions and realized plapping sounds kinda nice. Though I had my own idea of how to do it, it's safe to say it was intense, and by his words, surprisingly pleasurable. I still can't believe he actually got hard from that ... well ... "hard" , but you know what I mean 🤭

Also it's been a while since I wrote journal in second person, and I am still feeling aroused from the session, so I love to invite you into my mind and his body 😈 I want you to imagine this:

It's been over a month since I let you cum the last time. Actually, to be more precise, after you dribbled out of the cage like a total slut with an anal wand up your ass. But I admit, it was quite an orgasm. Well, the kind you can't experience with your penis 🤭 ... which kinda fits the theme of everything that followed.

I've been contemplating if I should let you at the start of the Locktober, but it was too close to the last time, so I've decided against it. I didn't want to spoil you 🤭 Ever since then, you've been spending your time in the tiniest cage I have for you that can be worn long-term. And on the rare occasion I swap you into something else, it's the flat one haha. But today you're in luck. You still get to enjoy the half-inch nub 😈 I know you're craving something more intense. It's been such a long time since you got to stretch out that small, steel hard chastity cage. Well, today's not the day, but I have other good news. I can slap your balls with a riding crop. That could make you feel something 🤭

I know your dick wasn't originally meant for any of this, but that's what makes it so hot. I love completely twisting your masculinity and reminding you that I can do absolutely anything with it, reshaping its purpose, and you're left with anything I let you have 🥵. I know that your dick was meant to get hard in the presence of a hot girl; it was meant for penetration, for making a big ol' mess, to fill pussies full of cum. But unfortunately I won't make you do any of that. You get squished, laughed at, your cum gets tossed into a bin, or you swallow it yourself and the only place you your dick has room to grow is deeper inside your body, as the cage won't budge. Haha 😈 I know you would do about anything, just for the chance to cum. Too bad. I am not giving you that chance.

What I am giving you is slapping your balls. And the best part is that you're that desperately horny that you're grateful for that. Good boy. 🥵 Enjoy the "edging", and don't try to think about all the other boys online and what they will do when they watch my boobs jiggle as I spank your ball with a crop. Don't think about all the cum, and how it would look on me. And certainly don't imagine the semen running in between my tits, over your chastity key.

Haha, you are really enjoying this, aren't you? I can see the bulge under the skin. That's pretty hot. I love how you're always spiraling deeper. There's no way you could ever have a regular vanilla sex is it? If you look at sexy girl, you're imagining how she would deny you, and how you could never put your dick inside her? I am right? Well, good. The best denial is the one you agree with. No matter the original purpose of it, your cock is meant to stay locked. You're meant to be pussyfree and dripping in the cage. I own you, and I love it, and I'll make sure that's what you'll get 😈
Well, it's not yet time for you to make your caged dribbles, so cool down your gooner fantasies and wait until your goddess decides it's time for you to leak more 🤭

[Jade malice @jade_malice]

And what are your plans for the weekend? If you don't have any, here's a tip. Lock yourself into the tiniest cage you have, buzz it with a vibrator and goon for hours, until you can't think straight 😈It will make the next two weeks more interesting 🤭

[goontube @goontube6969]

Mom catches son jerking off to her and then pegs him and fucks him
#motherson #momfucksson #sonfuckmom #taboo #anal #pegging #dildo #blowjob #bigtits #cum #dommymommy #analdildo

[MrHush @MrHush_88]

Estate agent gets fucked.

[Mads x Myles @MadsxMyles]

I love asking my friends to help tease!

[Sissy Queen Joyce 🏳️‍⚧️ @SissyJoyce]

I am so proud of myself! 🏳️‍⚧️👑
Yesterday, I got fucked by the King of Sissies 😚
I am so happy that I waited and I did it on my own terms.
The online preasure for ''not using a condom'' or ''getting fucked'' has been immense, and I am so glad I didn't do it for more likes or subscriptions. I didn't do it for you. I did it for myself. I wanted him. and I wanted it to be safe and it was magical. It was very special and very hot.
Everything has been filmed by a proffesional team, in high quality and I will also introduce them to you all soon. In Belgium, there is a person known as the mother of transgenders. She is a dominatrix and she is so good at producing content, a true artist! I am SO proud to say that I am under her wing. Then there is this incredible Trans & sissy transformation artist who does my styling, make-up and gave me a mountain of tips and tricks and takes good care of me. My looks are because of her. I am so happy, I am so lucky and by the end of the week, i'll introduce them all to you too because you all deserve to know them too.
So never, never give into the preasure of social media. I am so glad I did it on my own terms. I still have my soul.
I am real, I am the Queen of Sissies
And I love you all.
👑❤️

[Jade malice @jade_malice]

Feeding the desire, while taking out the ability 😈 I love how almost every guy in chastity is a complete gooner, always thinking sex and porn, precum dripping into underwear, but always craving more denial to make it even worse🤭When you're so deep down that orgasm feels like losing progress, you're on the right path 😈

[Hollie Hotwife | No PPV OF @holliehotwife]

Sissy chore day - it’s a hard life for them!

[𝐃𝐚𝐢𝐥𝐲 𝐂𝐮𝐜𝐤𝐨𝐥𝐝 (180k) @CuckoldEmpirex]

BBC Cuckold Session - Riley Reid

DM For Promos

[Jade malice @jade_malice]

Post orgasms play after long denial and edging is so mean 🤭

First, I made sure to do everything I could to make him as sensitive as possible. Chastity, teasing, denial and then long edging with enough oil, to make all nice and slippery. To make his dick feel like it's in heaven ... for a while 😈 Funny how things quickly change when I just don't stop.

This is the best post-orgasm play we had. I know a lot of people come and go, so many of you will see this for the first time. But some of you might find this session familiar, and you'd be right. It's from a second camera of a session we had a while ago. I have way too many unpublished takes like this that I feel would be a shame not to share with you 🥰

[Jade malice @jade_malice]

Short Story:
I wanted to see how horny he is after draining his prostate a few days ago 😈. Turns out, quite a bit, so that's amazing, and I can't wait to test more toys on him 🤭

Long Story:
I am seriously in love with prostate orgasm. One thing I've always disliked about male orgasm in general, no matter how fun it could be to watch a guy shake with pleasure, is that after it's done, there can be quite a bit of falling off. Post-nut clarity, as some call it, but often it feels more like a loss of interest. The "need" has been sated, so it's time to move on. But as a domme that craves the feeling and the interest, and if I am completely honest, the dependency as well, I am not that thrilled about it. 😈 I guess it's part of the reason why I am so drawn to denial, ruined orgasm, and all the other games one can play, that both make orgasm stronger when it comes to that, but also push it into the future, prolong the teasing, and create a very unique kind of intimacy that doesn't rely on finishing with orgasm every time.

After the prostate orgasm, I've felt that as well, and of course I've been asking him about it to better understand his feelings. It was one of the strongest orgasms he felt, but right after we were done, I could tell he was completely spent, drained, and satisfied, obviously with very little interest in playing more right away. But the recovery was surprisingly fast. I am quite positive that if it were a regular orgasm of the same intensity, it would take a lot longer to pick up the pace. 🥰 I feel quite curious and optimistic to figure out more about it. I wonder if it's more to do with denying him an erection the whole time, or the way he reached the orgasm. I guess, even if the orgasm was that intense, it wasn't "complete", as I kept him caged. There may be an urge that didn't get fulfilled, and I think that might be important. Not sure. I guess more research needs to go into it. 😈

Anyway, I was curious how eager he would be to get unlocked, so I could see what impact it had on him and how horny he is. Turns out, very! Yes! 😈 I was contemplating if I should really unlock the cage, or if I would just observe the straining against it, but I wanted to feel him, to squeeze him and properly edge him, so I could get a better idea of it. And I was glad I did. It was so hot to see him this worked up. 🥵 Haha, as soon as I unlocked the cage, he popped it off and was immediately hard. I am not sure I saw him wake up from the cage faster. Often he's rather slow after a longer lockup. I wonder if he was just excited to be close to my bare pussy, or if my previous treatment influenced that 🤭

Well, I got my answer basically instantly. He was super horny regardless of the orgasm he had a while back. So I did the only thing that came to my mind. I made it worse 🤭... or better. I guess that depends on a point of view. I edged him until I felt he was close. I love how he looks so eager and hard, resting over my pussy. Aw, I won't ever get tired of reminding him how long it's been since the last time inside me. And I let the "last time" linger a bit, to be a little vague about what I mean by it.😈

Often I edge him until I feel he can't nearly take it anymore. This time I wanted him to crave a lot more. I just wanted to see him out of the cage for a while, since lately he wasn't getting much freedom. And with Locktober around the corner, I don't think it's going to get much better in the future. So, I let him stretch out, reminded him that his dick is still capable of it, so he remembers it well once he's squished in the cage and possibly cumming on my dildo 🤭. The contrast is half the fun 🥰